Photoredox cobalt-catalyzed regio-, diastereo- and enantioselective propargylation of aldehydes via propargyl radicals

[1]  Z. Shi,et al.  Cr-Catalyzed Regio-, Diastereo-, and Enantioselective Reductive Couplings of Ketones and Propargyl Halides , 2023, ACS Catalysis.

[2]  Gongqiang Li,et al.  Regio- and Stereoselective Reductive Coupling of Alkynes and Crotononitrile. , 2022, Journal of the American Chemical Society.

[3]  Chang Guo,et al.  Nickel-catalyzed switchable 1,3-dienylation and enantioselective allenylation of phosphine oxides , 2022, Nature Communications.

[4]  Chang Guo,et al.  Nickel-Catalyzed Asymmetric Propargylation for the Synthesis of Axially Chiral 1,3-Disubstituted Allenes. , 2022, Journal of the American Chemical Society.

[5]  Yidong Wang,et al.  Enantioselective and Diastereodivergent Allylation of Propargylic C-H Bonds. , 2022, Journal of the American Chemical Society.

[6]  Junliang Zhang,et al.  Catalytic Asymmetric Axially Chiral Allenyl C-P Bond Formation. , 2022, Journal of the American Chemical Society.

[7]  Wenxin Lu,et al.  Corrigendum: Cobalt-Catalyzed Regio-, Diastereo- and Enantioselective Intermolecular Hydrosilylation of 1,3-Dienes with Prochiral Silanes. , 2022, Angewandte Chemie.

[8]  Wenxin Lu,et al.  Cobalt-Catalyzed Regio-, Diastereo- and Enantioselective Intermolecular Hydrosilylation of 1,3-Dienes with Prochiral Silanes. , 2022, Angewandte Chemie.

[9]  Hao Jiang,et al.  Photoassisted Cobalt-Catalyzed Asymmetric Reductive Grignard-Type Addition of Aryl Iodides. , 2022, Journal of the American Chemical Society.

[10]  Chang Guo,et al.  Combining nickel and squaramide catalysis for the stereodivergent α-propargylation of oxindoles , 2022, Nature Synthesis.

[11]  W. Xiao,et al.  Construction of axial chirality via asymmetric radical trapping by cobalt under visible light , 2022, Nature Catalysis.

[12]  Chang Guo,et al.  Ni/Chiral Sodium Carboxylate Dual Catalyzed Asymmetric O-Propargylation. , 2021, Journal of the American Chemical Society.

[13]  Zhenyang Lin,et al.  Enantioselective Copper-Catalyzed Radical Cyanation of Propargylic C-H Bonds: Easy Access to Chiral Allenyl Nitriles. , 2021, Journal of the American Chemical Society.

[14]  Fanke Meng,et al.  Cobalt-catalyzed atom-economical, diastereo- and enantioselective coupling of aldimines and cyclopropanols , 2021, Science China Chemistry.

[15]  Fanke Meng,et al.  Cobalt-Catalyzed Diastereo- and Enantioselective Reductive Allyl Additions to Aldehydes with Allylic Alcohol Derivatives via Allyl Radical Intermediates. , 2021, Journal of the American Chemical Society.

[16]  Ji‐Bao Xia,et al.  Highly Regio- and Enantioselective Reductive Coupling of Alkynes and Aldehydes via Photoredox Cobalt Dual Catalysis. , 2021, Journal of the American Chemical Society.

[17]  Chang Guo,et al.  Collective synthesis of acetylenic pharmaceuticals via enantioselective Nickel/Lewis acid-catalyzed propargylic alkylation , 2021, Nature communications.

[18]  Liming Zhang,et al.  Gold-catalysed asymmetric net addition of unactivated propargylic C–H bonds to tethered aldehydes , 2021, Nature Catalysis.

[19]  S. Wheeler,et al.  Optimization of Catalyst Structure for Asymmetric Propargylation of Aldehydes with Allenyltrichlorosilane , 2020 .

[20]  Fanke Meng,et al.  Cobalt-Catalyzed Diastereo- and Enantioselective Hydroalkylation of Cyclopropenes with Cobalt-Homoenolates. , 2020, Angewandte Chemie.

[21]  J. Antilla,et al.  Bi(cyclopentyl)diol-Derived Boronates in Highly Enantioselective Chiral Phosphoric Acid-Catalyzed Allylation, Propargylation and Crotylation of Aldehydes. , 2020, The Journal of organic chemistry.

[22]  Fanke Meng,et al.  Cobalt-catalyzed diastereo- and enantioselective allyl addition to aldehydes and α-ketoesters through allylic C–H functionalization , 2020, Cell Reports Physical Science.

[23]  Amy K. Cain,et al.  Nontoxic Cobalt(III) Schiff Base Complexes with Broad‐Spectrum Antifungal Activity , 2020, Chemistry.

[24]  Junliang Zhang,et al.  Pd-Catalyzed Enantioselective Syntheses of Trisubstituted Allenes via Coupling of Propargylic Benzoates with Organoboronic Acids. , 2020, Journal of the American Chemical Society.

[25]  H. Tsuji,et al.  Nickel-Catalyzed Asymmetric Friedel-Crafts Propargylation of 3-Substituted Indoles with Propargylic Carbonates Bearing an Internal Alkyne Group. , 2020, Organic letters.

[26]  Yun‐He Xu,et al.  Catalytic Asymmetric Conjugate Protosilylation and Protoborylation of 2-Trifluoromethyl Enynes for Synthesis of Functionalized Allenes. , 2020, Organic letters.

[27]  G. C. Fu,et al.  Catalyst-controlled doubly enantioconvergent coupling of racemic alkyl nucleophiles and electrophiles , 2020, Science.

[28]  Lian-rui Hu,et al.  Enantioselective Synthesis of Multisubstituted Allenes by Cooperative Cu/Pd-Catalyzed 1,4-Arylboration of 1,3-Enynes. , 2019, Angewandte Chemie.

[29]  Chaofan Huang,et al.  Tetrasubstituted allenes via the palladium-catalysed kinetic resolution of propargylic alcohols using a supporting ligand , 2019, Nature Catalysis.

[30]  W. Xiao,et al.  Exploration of Novel Chiral Cobalt Catalyst for Visible-Light-Induced Enantioselective Radical Conjugate Addition. , 2019, Angewandte Chemie.

[31]  W. Xiao,et al.  Exploration of a Chiral Cobalt Catalyst for Visible‐Light‐Induced Enantioselective Radical Conjugate Addition , 2019, Angewandte Chemie.

[32]  Fanke Meng,et al.  Co-Catalyzed Diastereo- and Enantioselective Hydroalkenylation of Cyclopropenes with Alkenylboronic Acids. , 2019, Angewandte Chemie.

[33]  S. Buchwald,et al.  Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes , 2019, Journal of the American Chemical Society.

[34]  Tongtong Wang,et al.  Cobalt‐Catalyzed Diastereo‐ and Enantioselective Hydroalkenylation of Cyclopropenes with Alkenylboronic Acids , 2019, Angewandte Chemie.

[35]  Lei Zhu,et al.  Asymmetric Propargylic Radical Cyanation Enabled by Dual Organophotoredox and Copper Catalysis. , 2019, Journal of the American Chemical Society.

[36]  T. Sengoku,et al.  Indium- and zinc-catalyzed enantioselective amide propargylation of aldehydes with stannylated allenyl amides. , 2019, Organic & biomolecular chemistry.

[37]  Shuo-qing Zhang,et al.  Catalytic asymmetric synthesis of chiral trisubstituted heteroaromatic allenes from 1,3-enynes , 2018, Communications Chemistry.

[38]  M. Krische,et al.  Catalytic Enantioselective Carbonyl Propargylation Beyond Preformed Carbanions: Reductive Coupling and Hydrogen Auto‐Transfer , 2018, ChemCatChem.

[39]  H. Tsuji,et al.  Nickel-Catalyzed Asymmetric Propargylic Amination of Propargylic Carbonates Bearing an Internal Alkyne Group. , 2018, Organic letters.

[40]  E. Miliordos,et al.  Enantioselective Syntheses of Homopropargylic Alcohols via Asymmetric Allenylboration. , 2018, Organic letters.

[41]  S. Ge,et al.  Copper-catalyzed asymmetric hydroboration of 1,3-enynes with pinacolborane to access chiral allenylboronates , 2018 .

[42]  J. del Pozo,et al.  Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates. , 2018, Journal of the American Chemical Society.

[43]  K. S. Egorova,et al.  Toxicity of Metal Compounds: Knowledge and Myths , 2017 .

[44]  S. W. Kim,et al.  Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier. , 2017, Accounts of chemical research.

[45]  S. Ma,et al.  Palladium-Catalyzed Enantioselective Alkoxycarbonylation of Propargylic Carbonates with (R)- or (S)-3,4,5-(MeO)3 -MeOBIPHEP. , 2017, Chemistry.

[46]  M. Krische,et al.  Ruthenium‐BINAP Catalyzed Alcohol C—H tert‐Prenylation via 1,3‐Enyne Transfer Hydrogenation: Beyond Stoichiometric Carbanions in Enantioselective Carbonyl Propargylation. , 2016 .

[47]  S. Buchwald,et al.  Copper-catalyzed asymmetric addition of olefin-derived nucleophiles to ketones , 2016, Science.

[48]  L. Cavallo,et al.  SambVca 2. A Web Tool for Analyzing Catalytic Pockets with Topographic Steric Maps , 2016 .

[49]  M. Krische,et al.  Ruthenium-BINAP Catalyzed Alcohol C-H tert-Prenylation via 1,3-Enyne Transfer Hydrogenation: Beyond Stoichiometric Carbanions in Enantioselective Carbonyl Propargylation. , 2016, Journal of the American Chemical Society.

[50]  X. Zhang,et al.  Synthesis of Highly Substituted Racemic and Enantioenriched Allenylsilanes via Copper-Catalyzed Hydrosilylation of (Z)-2-Alken-4-ynoates with Silylboronate. , 2015, Journal of the American Chemical Society.

[51]  D. Gryko,et al.  Vitamin B12 catalysed reactions. , 2015, Chemical Society reviews.

[52]  Fanke Meng,et al.  Diastereo- and Enantioselective Reactions of Bis(pinacolato)diboron, 1,3-Enynes, and Aldehydes Catalyzed by an Easily Accessible Bisphosphine–Cu Complex , 2014, Journal of the American Chemical Society.

[53]  C. Vidal,et al.  Glycerol: a biorenewable solvent for base-free Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides with terminal and 1-iodoalkynes. Highly efficient transformations and catalyst recycling , 2014 .

[54]  Wanli Zhang,et al.  A room-temperature catalytic asymmetric synthesis of allenes with ECNU-Phos. , 2013, Journal of the American Chemical Society.

[55]  W. Roush,et al.  Chiral Brønsted Acid Catalyzed Enantioselective Synthesis of anti-Homopropargyl Alcohols via Kinetic Resolution-Aldehyde Allenylboration Using Racemic Allenylboronates. , 2013, Organic letters.

[56]  W. Roush,et al.  Chiral Brønsted acid catalyzed enantioselective synthesis of anti-homopropargyl alcohols via kinetic resolution-aldehyde allenylboration using racemic allenylboronates. , 2013, Organic letters.

[57]  M. Krische,et al.  Enantioselective carbonyl propargylation by iridium-catalyzed transfer hydrogenative coupling of alcohols and propargyl chlorides. , 2012, Angewandte Chemie.

[58]  C. Bolm,et al.  Synthesis of N-Methyl-2-indolyl- and N-Methyl-2-benzo[b]furyl-Substituted Sulfoximines by Pd/Cu Co-Catalyzed Domino Cross-Coupling/Cyclization Reactions , 2012 .

[59]  Shichao Yu,et al.  Allenes in catalytic asymmetric synthesis and natural product syntheses. , 2012, Angewandte Chemie.

[60]  Joyce C. Leung,et al.  Diastereo- and enantioselective iridium-catalyzed carbonyl propargylation from the alcohol or aldehyde oxidation level: 1,3-enynes as allenylmetal equivalents. , 2012, Angewandte Chemie.

[61]  Hao Wang,et al.  Brønsted acid catalyzed asymmetric propargylation of aldehydes. , 2012, Angewandte Chemie.

[62]  G. C. Fu,et al.  Nickel-catalyzed enantioselective cross-couplings of racemic secondary electrophiles that bear an oxygen leaving group. , 2012, Journal of the American Chemical Society.

[63]  L. R. Reddy.  Chiral Brønsted acid catalyzed enantioselective propargylation of aldehydes with allenylboronate. , 2012, Organic letters.

[64]  M. Sigman,et al.  Three-Dimensional Correlation of Steric and Electronic Free Energy Relationships Guides Asymmetric Propargylation , 2011, Science.

[65]  B. Trost,et al.  Ligand-accelerated enantioselective propargylation of aldehydes via allenylzinc reagents. , 2011, Organic letters.

[66]  B. Captain,et al.  Helical chiral 2,2'-bipyridine N-monoxides as catalysts in the enantioselective propargylation of aldehydes with allenyltrichlorosilane. , 2011, Organic letters.

[67]  X. Hou,et al.  Catalytic asymmetric propargylation. , 2011, Chemical reviews.

[68]  D. Usanov,et al.  Asymmetric Nozaki-Hiyama propargylation of aldehydes: enhancement of enantioselectivity by cobalt co-catalysis. , 2010, Angewandte Chemie.

[69]  Jinhua J. Song,et al.  Copper catalyzed asymmetric propargylation of aldehydes. , 2010, Journal of the American Chemical Society.

[70]  Songbai Liu,et al.  Catalytic enantioselective Cr-mediated propargylation: application to halichondrin synthesis. , 2009, Organic letters.

[71]  Sukbok Chang,et al.  Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water. , 2005, Journal of the American Chemical Society.

[72]  M. Nakada,et al.  Studies on Catalytic Asymmetric Nozaki—Hiyama Propargylation. , 2004 .

[73]  M. Nakada,et al.  Studies on catalytic asymmetric Nozaki-Hiyama propargylation. , 2004, Organic letters.

[74]  S. Hashimoto,et al.  Selective synthesis of optically active allenic and homopropargylic alcohols from propargyl chloride , 2002 .

[75]  J. Tedrow,et al.  Highly enantioselective syntheses of homopropargylic alcohols and dihydrofurans catalyzed by a bis(oxazolinyl)pyridine-scandium triflate complex. , 2001, Journal of the American Chemical Society.

[76]  S. Denmark,et al.  Lewis base activation of Lewis acids: catalytic enantioselective allylation and propargylation of aldehydes. , 2001, Journal of the American Chemical Society.

[77]  Xiaoming Chen,et al.  Asymmetric synthesis of homopropargylic alcohols from aldehydes and allenyltri-n-butylstannane , 1994 .

[78]  W. Xiao,et al.  Application of Propargylic Radicals in Organic Synthesis , 2019, Acta Chimica Sinica.

[79]  Sook-Kyung Yoon,et al.  CATALYTIC ASYMMETRIC PROP-2-YNYLATION INVOLVING THE USE OF THE BIFUNCTIONAL SYNERGETIC REAGENT ET2BSPRI , 1997 .

[80]  C. Brown,et al.  “P-2 nickel” catalyst with ethylenediamine, a novel system for highly stereospecific reduction of alkynes to cis-olefins , 1973 .